Heir to one of the principal gentry inheritances in the north-west, Pennington had a brief but active career. On 31 Oct. 1440 he joined his maternal uncle, John Tunstall*, in offering heavy security for the appearance of his first cousin, Thomas Haryngton II*, before the King. Here he is described as ‘of Ravenglass’ near Muncaster, perhaps by virtue of property settled upon him by his father on his marriage to the daughter of another Cumberland knight. Soon after, he departed for France, continuing his family’s well-established military tradition. On 26 May 1441 he mustered in the retinue of Richard, duke of York, lieutenant-general of France, and sailed a month later.
It may be that in the following year Pennington was with his father in the force commanded by the earl of Northumberland’s son, Henry Percy, Lord Poynings, which met defeat at the hands of the Scots on the river Sark on 23 Oct. 1448; and it would be consistent with all else that is known of him if he took part in the disastrous French campaign of 1449-50.
